
Vacation rentals with a pool in Dewey Beach
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Top-rated rentals with a pool in Dewey Beach
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Newly Renovated Modern 2 Bed/2 Bath Condo w/ Pool
Newly renovated and designer decorated 2 bedroom/2 bath beach condo with the most comfortable beds imaginable. Located in the heart of Dewey Beach with an outdoor pool and only 1 block to beach and bay. One bedroom includes a King sized bed with private bathroom. The 2nd bedroom includes a Queen and a Twin sized beds adjacent to the 2nd bathroom. The fully equipped kitchen features stainless steel appliances, granite countertops, an island w/ seating, and washer/dryer. 2 parking spots included.
4.98 out of 5 average rating, 125 reviews
Beautiful waterview 2B condo w/Dock&Close to Beach
Welcome to the Canal Bungalow! A stylish 1000 sq. foot retreat to enjoy all the fun & relaxation of the coastal lifestyle in North Oc. Bring your boat with you and dock alongside your back porch, enjoy pool access in a private gated community, or bring your sports gear for Northside Park. We are tucked away on the quiet bayside of OC & only a few minutes walk to the beach. Unwind on our beautiful balcony while watching the boats go by & finally understand the true meaning of a coastal lifestyle!
5.0 out of 5 average rating, 122 reviews
Coastal Modern Condo • Balcony, 2 Baths, East Rt 1
☀️ Your Rehoboth Beach Escape Why guests love staying here: • Community pool 🌴 • 2 full baths • Private screened balcony 🌿 • East of Route 1 • Strong central AC ❄️ • Split-bedroom layout for added privacy • Beach chairs & towels included 🏖️ • Fast WiFi + smart TVs • Plenty of FREE parking • In-unit washer & dryer • Minutes to beaches, boardwalk, restaurants & shopping • Quiet community close to everything Perfect for couples, families, remote workers, girls’ weekends, and relaxing getaways.
4.99 out of 5 average rating, 121 reviews
Downtown RB Townhome-Great Location-WALK TO BEACH
Great location in downtown Rehoboth Beach-walk everywhere! Tucked away in a quite residential community, yet close to all of RB's favorite attractions: 4 blocks to the beach and boardwalk, less than 1/2 block to Rehoboth Avenue. No need to drive once you arrive-walk to the beach, boardwalk, Funland, and all of the restaurants and shopping in town. Also close to the bike trails. This 2 level townhome overlooks the salt water pool and includes 2 parking spaces and 2 additional parking passes.
4.91 out of 5 average rating, 238 reviews
Cozy Rehoboth Beach Condo w/ 2 bedrooms
This condo is a boho getaway tucked away in a quiet enclave conveniently located on the beachside of Highway 1. It has dedicated parking in front, plus an additional spot for a second car. This condo it is a two bedroom/two bathroom unit. Full kitchen and a dining area that seats up to six. The condo is on the second floor with one stair flight. The beach is a 20 minute walk, 10 minute bike ride, or 5 minute drive Community pool on site provides an extra place to relax and cool down.
4.99 out of 5 average rating, 181 reviews
Perfect Rehoboth Beach Getaway with Hot Tub
Discover the epitome of coastal comfort in newly remodeled home. Dive into luxury with a private hot tub, where the bubbling warmth provides the perfect escape. Unwind in the chic interiors, adorned with modern furnishings. Stay connected with complimentary Wi-Fi as you plan your outings to the nearby beaches, bustling boardwalk, and local attractions. Steps away from tax free outlet shopping. With convenience at every turn, this home ensures a perfect blend of tranquility and accessibility.
4.94 out of 5 average rating, 109 reviews
Modern Beach House w/ Private Pool
Modern eco-friendly retreat perfect year-round! This salt-box cottage is an open concept 3 bedroom, 2 bathroom filled with natural light. Huge yard with a pool house with dining table and grill, patio with lounge chairs, outdoor shower, and private pool (pool open May 15 - October 15). Located perfectly for Rehoboth Beach or Dewey Beach visitors. It is a 20 minute walk to the shops and restaurants on Rehoboth Ave or to the beach. Three parking spots, beach items, and all amenities included.
4.97 out of 5 average rating, 103 reviews
The Jungalow - Dog Friendly, Fenced in & Pool
Centrally and peacefully located. Find yourself immersed in a thoughtfully designed vacation space where the relaxing days don’t end at the beach. Dog friendly (2), community pool, walkable to restaurants, bus stop, outlets, and local bars! Fenced in yard perfect for kiddos and pups while grownups can relax on the porch! Also, a comfortable space to enjoy a movie night in or relax outside under the stars. Our little slice of paradise is waiting for you, your guests and well behaved doggies!
5.0 out of 5 average rating, 101 reviews
Luxury water-view condo with high-end finishes
Luxury 2-bedroom condo at The Residences at Lighthouse Cove located in the heart of Dewey Beach. This unit features great views of Rehoboth Bay and is only 1 block from the Atlantic Ocean. Easy walk to Dewey Beach’s shops, restaurants, and nightlife. This unit sleeps up to 6. There is a master bedroom with a king bed and ensuite bathroom. The second bedroom has a queen bed. There are 2 twin-size fold-away beds. Lounge at private rooftop pool, fire pits, & grills for Residences
4.95 out of 5 average rating, 154 reviews
Oceanfront Condo w/ Resort Amenities 3BDR &3pools
Sea Watch Condo's is an ideal family location with tons of amenities. The until is a recently updated 3 bedroom 2 bathroom condo that sleeps 6 people in 2 queen beds, 2 twin beds . The unit is ocean front with a large oceanfront balcony. The amenities Include, basketball court, tennis courts, playground, arcade, movie theater, billiard room, indoor pool and outdoor pool as well as a restaurant. The condo has 24 hour security and plenty of parking. Pools closed in off season
4.88 out of 5 average rating, 146 reviews
Dodd House Beach Home w/private pool and hot tub
Saturday to Saturday bookings from the third week in June through mid August. Large 5 bed 3.5 Bath Luxury Home with pool and hot tub. Parking for six to eight cars. ARRIVE, STOCK UP, AND NEVER LEAVE IF YOU CHOOSE! GET YOUR FAMILY AND FRIENDS TOGETHER SAFELY! This large 4,500 square foot rental unit includes 5 private BR, 3.5 BTH, and sleeps 18! Pool opens May 15th until September 30th. Outdoor fire pit with some wood provided. 25 and older please.
4.88 out of 5 average rating, 250 reviews
Mid century vacation condo newly renovated.
Enjoy a stylish experience at this centrally-located place. Expansive ocean views, fully renovated space with tasteful details and a serene palette to maximize your well deserved peaceful vacation time. Walk distance to a great variety of high-end restaurants and beach treasures, gift shops, ice cream parlor and games next door. The unit includes a free parking spot in the building. Enjoy brand new bedding and mattresses and everything else.
4.96 out of 5 average rating, 114 reviewsPopular amenities for Dewey Beach rentals with a pool
House rentals with a pool

Hot tub, Pool, Shop & Dine, Sleeps 8
4.94 out of 5 average rating, 187 reviews
Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB
4.93 out of 5 average rating, 290 reviews
3 BR Waterfront Home, Minutes to the Beach
4.93 out of 5 average rating, 152 reviews
Bright Open Floor Plan Family Beach Retreat
4.91 out of 5 average rating, 149 reviews
The Big Chill at Bethany Beach
4.98 out of 5 average rating, 105 reviews
4BD 4BA Carriage Home-Fenced Yard | Rehoboth Beach
4.9 out of 5 average rating, 135 reviews
Gorgeous 5BR, 4.5BA, in town, pool, hot tub, beach
4.96 out of 5 average rating, 56 reviews
Family & Pet-friendly Beach House with Pool
5.0 out of 5 average rating, 31 reviewsCondo rentals with a pool

Direct Oceanfront with a View and Amenities Galore
4.94 out of 5 average rating, 339 reviews
Right on Silver Lake walk to beach!
4.8 out of 5 average rating, 331 reviews
Renovated Condo Near Outlets, 3.5 Miles to Beach
4.98 out of 5 average rating, 226 reviews
Beautiful Updated Condo Waterfront, Pool, Sunsets
4.91 out of 5 average rating, 101 reviews
Modern & Cozy Retreat | Pool | Close to Beaches
4.95 out of 5 average rating, 327 reviews
Cozy Creekwood Condo - Relaxing Getaway - W/ Pool
4.98 out of 5 average rating, 310 reviews
Stress-Free Family Beach Stay | Pool + Kid Perks
4.99 out of 5 average rating, 183 reviews
Sunrise Studio - Ocean Front, on Boardwalk, Pool!
4.94 out of 5 average rating, 202 reviewsOther vacation rentals with a pool

Coastal Comfort at the Beach, Sleeps 4, *w/ Pool
5.0 out of 5 average rating, 29 reviews
Recently Updated 2 bed -2 bath in heart of Dewey
4.97 out of 5 average rating, 78 reviews
Bayview Oasis-Pool/Free Parking
4.9 out of 5 average rating, 50 reviews
Golden Hour Getaway | Marina & Bay Views in Dewey
4.98 out of 5 average rating, 48 reviews
Luxury Bayfront Condo Only 1 Block from the Ocean!
4.89 out of 5 average rating, 57 reviews
*Walk to the Beach* Ocean Block Condo - Pool
4.95 out of 5 average rating, 93 reviews
Cozy Coastal Haven: Beach Community Charm
4.98 out of 5 average rating, 96 reviews
Ruby's Retreat at the Beach
4.84 out of 5 average rating, 32 reviewsDestinations to explore
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